Aaron Strauss: You're listening to The Dealmakers' Edge with A.Y. Strauss, diving deep into stories behind commercial real estate leaders.

Hello, everyone, and welcome to The Dealmakers' Edge. Today, I'm excited to be joined by Norman Bobrow, who is president of Norman Bobrow & Co., Inc., one of New York's leading independently-owned, tenant-focused commercial real estate brokerages.

A third-generation real estate professional and lifelong New Yorker, Norman launched the firm in 1980 with a clear mission to represent tenants exclusively and deliver results with precision, integrity, and relentless advocacy. Over the course of his career, he's personally negotiated more than 3,000 leases and overseen the acquisition of more than 300 properties nationwide. He's built a fabulous reputation as someone with integrity, with deep expertise, and someone who has also built a great team.

He's invested in many deals personally. He's invested in a ton of relationships and built a great culture at his organization. He's been a good friend to me personally. So I'm really excited for this conversation where we talk about his life's journey, his struggles from an early age, how he's dealing with present day issues, how he's navigated, how he's grown his career, and his life philosophy of giving back and being philanthropic and never making it about yourself, making it about other people.

So here we go with the episode. I hope everyone enjoys.

Hello, everyone, and welcome to The Dealmakers' Edge. Today, we are very excited to be joined by my good friend, Norman Bobrow. I think we have known each other for close to 17, 18 years, really going back.

So you've tolerated my presence in your life all these years. Thank you for that. I'm honored you took some time to share your story, which is a terrific story, which is always constantly growing and evolving. For people who don't know you, and obviously, they've heard your bio, but maybe you can give a background. We'll go back to your roots for a few minutes, and then we'll start to gradually bring to present day, if you don't mind.

Norman Bobrow: I was born in Queens, one of four, two brothers are physicians. My sister was a computer programmer. I was dyslexic, totally couldn't read till the eighth grade. I was in private school. After private school, luckily, my parents saw that there was a problem, and I was very lucky.

At one point, my parents were saying, "We've got to set Norman up in a store." They changed their will to give me more because they thought I could never survive. I was very interested in horticulture. I went to college for horticulture, where I got into the college because my brother-in-law wrote the best letter.

I did well there. I left Alfred because of anti-Semitism. I always say, "God didn't want me to take this path." I made a left turn. I then came here, worked in a major public company starting at the very, very bottom called Syntex Corporation, built the Winston Towers, and learned.

But I suddenly saw that it was impossible for me to make money unless I traveled to other states. Basically, it just didn't seem to be a great way for me to grow entrepreneurially because I didn't have the money to really build. My father was already retired. I was born when he was 40, so when I was 20, he was 60.

I joined the National Guard, avoiding going to Vietnam. I went to college here, but at that time, college was crazy because of the Vietnam War. I ended up dropping out of college here again after I transferred from Alfred. I went to college at night, 12 months a year, to get that piece of paper, which my cousin Josh Musk suggested I do.

I got it in 12 months, going 12 months a year to get that piece of paper that I have a college degree, which I actually do value because it gave me a lot of insight into certain areas like money and banking, advertising, marketing, and different courses that I took. So I don't regret anything. I also was in the National Guard one weekend a month for six years, at the same time working in construction for Syntex in New Jersey, building the Winston Towers, the Palace Stadium, 200 Tower, and the 300 Tower.

I saw that they wanted to send me now to Florida, and I said, "You know what, I think I need to make a change." I went to a headhunter who suggested, "Why don't you try brokerage?" Actually, I started with another firm called IEC Properties and was building up in Rockland County.

I rented all the space very quickly, and they gave me a pat on the back. "When we start the next building, we'll give you a raise." So I suddenly said, "This is not going to work." I made them a couple of million dollars on this industrial park because I rented it to office tenants.

So I went to Paula Burns, who was then a top person who placed people, and she placed me and said, "Why don't you try brokerage?" She said, "I can get you a job with all the big firms, but I think you should try brokerage." I took the challenge. It was a big success.

I worked for a very successful broker, Richard Schlesinger, who was doing monster deals. He had a very small office, very low-budget operation. I was his top broker. I felt the time was for me to go on my own because he was very limited in his whole operation.

He had one person who covered the entire office and the phones, everything, and just didn't want to really do more than his own business. So I opened up my own shop and was booming from there. People joined me, and I grew, and now I'm at 25 leasing brokers.

At the same time, I also was involved with investments. I come from a real estate family where my mother's siblings all were in real estate. It was the Musk family. I got involved in experiences where my father would do small syndications. I was lucky enough to watch him participate in those syndications and do my brokerage business and also invest at the same time.

I follow only a few people out there. My biggest follower was Warren Buffett, just giving me certain advice that he gave to everybody out there, which was the most amazing. I was lucky enough to go visit him where he said, "Don't leverage yourself more than 60%. Don't buy companies that you think are going to just be involved in one state or one continent. Go to like Coca-Cola." It jumped the waters to different continents.

So I learned from him and my dad and from seeing all the situations of family members that had made it and lost it, and what happened, why they did that. I've grown to be a very busy brokerage firm in the city of New York, where we do close to about 200 to 250 leases a year. But we are not a factory.

We give each tenant personal care. We look to do a deal, looking for every aspect, how we can make a very good deal for the tenant side. My firm is a little different than other firms like Newmark, Cushman, or CBRE. These people represent both sides, JLL, both sides. We represent the tenant.

Unless it's a family property that I'm working on, we really don't take on agencies of other people. You can't, just like an attorney, when he takes on a case, he says, "I want to be sure there's no conflict here." So we took the tenant's side. We could have taken the landlord's side, but we took the tenant's side, and we sit there and fight to get the best deal for the tenant.

Although we bring them to, we want to get the best deal. A number of times, I'll tell a tenant, "This is a difficult landlord to deal with. Maybe a lower price, and maybe you want to be here." I did a number of deals where tenants took lower prices, even though it was a difficult landlord, and they've been happy.

One tenant has been in the same building for over 38 years and has never had a problem with that landlord, where other people will knock him. His loss factors were lower. His deal was better. That's basically what my job is.

So we run this like a family business. I hear everyone's personal stories. I try to be there for everybody. I still enjoy coming to the office. I'm here five days a week.

I don't sleep here anymore, which I never did. But I try to get out by 6 o'clock. I leave the house at 6:30 in the morning and get here, and just try to do the best I can for everybody. It's a team. What's a little unique about our firm is that everyone likes each other.

People will give people ideas. We have two meetings a week. One is a space and market meeting where we go in the conference room and I talk about all the things going on out there in the industry, whether it's a new building going up, whether it's a landlord that's in default, or whether it's something happening in the financials, markets that are affecting all real estate people. Then the other meeting is we give a training class, which again, is mandatory for the younger brokers.

A number of the older brokers don’t, of course, attend anymore, but we try to train you, tell you how to measure space, how to explain space. Don’t hold anything back. If there’s a negative, tell the negative. Just try to give people how to be a first-class broker and be honorable out there.

Aaron Strauss: Well said. We’ve had the privilege of doing a training session in your office too on some legal leasing issues, so thanks for inviting us in fairly recently. What prompted you to take the path of really building out a firm? You have the skills on your own. You’ve got a lot of people that you’re dealing with, you’re training, you’ve mentored a whole generation or two of young, outstanding brokers.

You give very generously of your time, not only generously financially to a lot of great causes, but you’re really there for a lot of people. You could have taken the road of just saying, “Let me work with a couple of people, an office manager, do my own deals.” What prompted you to want to develop this whole team and culture and kind of family vibe?

Norman Bobrow: First of all, one of the biggest things you can do for someone is help them learn how to make a living. It’s not giving, yes, I am the treasurer of a school. I am very involved in many charities, and charity is on top of my list, more important than anything else. Matter of fact, I was negotiating with Larry Silverstein for two floors in the World Trade Center, and there was a conflict on the brokerage commission.

I asked Larry, “How about if we just gave this to charity?” And he said, “Norman, I can’t do that.” That’s my biggest goal, helping people learn how to make a living. Yes, it’s important for the company to be strong and make money, but I’m very happy when I see someone who’s out there and maybe they weren’t an A student in school, maybe they have a small speech impediment, or whatever it is, and try to get them to see, “Wow, here’s an opportunity where you can make a living, pay for your kids’ education, and have a nice life.”

That probably comes from a couple of reasons. My mother was a non-paid employee fundraiser for United Cerebral Palsy, which she gave 50 years, luckily, she lived to 103, over 50 years of her time helping kids with cerebral palsy. I also saw tremendous philanthropy from my grandparents, where my grandfather built many institutions in Brooklyn. So I always said, “I want to give back.” How do you give back? How do you teach this? So I try to teach that to my brokers.

I feel it’s a good feeling. I have that same mentality as Warren Buffett had. I have one house, two cars. If I want to go to a nice hotel, I go to a nice hotel. I don’t need all the extra fringes in life. To me, helping someone get a high school education, helping someone pay for their grammar school education, those are the important things to me in life, not having something material.

Aaron Strauss: Yeah. I think your philosophy, you articulated it once, just always look forward. Look forward all the time. Not to the left, not to the right. Don’t look back. It’s driven by your upbringing. Let’s face it, everybody struggles, but it’s just an enormous amount of resilience you need in life to do thousands of leases, with everyone of them on the backs of probably 15 to 20 deals that didn’t materialize, and to work with tons of different interesting personalities in the city of New York and beyond.

Norman Bobrow: Yes. I will correct myself, by the way. I was very successful. My parents changed the will back to everyone getting an equal share. I take care of the investments for a lot of people. I oversee a lot of different trusts and stuff where people will say, “Norman, I want you to be the trustee for my kids,” or something like that. So you never know where your life is going to be. You don’t have to be the smartest person.

I will say what’s so remarkable is that on the computer, there’s a function called “Read Out Loud.” My reading is not great, but I can read a lease, put it into Word, and I can read it out loud as fast as I want to read it or a commission agreement. I also learned something, the school I am, we had an Israeli night, and Israel came out with a thing called OrCam Read. It’s a small device five size the size of a pen, and you can point it to any page and it’ll read it to you as fast as you want it to read it to you.

So I go through the Wall Street Journal—the entire journal—reading it with this little device that reads out loud, clear as can be, and it’s just amazing device. Today, even if you have some learning disabilities, you can be a superstar out there. The whole thing is to try to be yourself, be honest, and always think, I always say to someone, “There’s a tree in front of me, but I can see behind the tree.”

When you have, like me, a little bit dyslexic, you see things that other people don’t see because you had to fight so hard to get to every step of your life. Thank God I haven’t had too many setbacks.

Aaron Strauss: Thank God. If you're in a training session with some of your brokers, and you have some really fabulous brokers, many of which who I've met and dealt with. So you've really been a great mentor to some fabulous people and continue to be. What are those core philosophies? We're hitting on them, but new broker starts and they say, "Norman, give me the 10 commandments." You know, besides being honorable, first-class integrity, treat people the right way, be honest, show up.

A lot of younger people don't always want to show up. I know you're in their office five days a week, which is very anachronistic, but it's becoming a trend again. What are the core philosophies you're laying down in those first few months of somebody who says, "I want to make it in brokerage in New York. I want to make it in business. I want to make it in life."

Norman Bobrow: So first of all, you have to find something that you enjoy. If you don't enjoy what you're doing, change your career. Don't sit there and suffer your whole life. "I hate my job. I hate the people I work for. I hate coming to work." When a guy says to me, "Norman, all I'm doing is thinking about the office all day long. I love this business because it's so entrepreneurial and the sky's the limit," I try to explain to brokers, you have to understand there's 500 million square feet of space in New York City.

With an average of a lease saying 10 years, that means 50 million square feet turnover. Tenants have no idea how to, landlords can't find tenants because they own their property. They don't have a way to go calling people, so they need us. So you, as a broker, have to be out there finding those tenants.

Now, years ago, I knocked on doors. I made lists and lists and put them on index cards and then filed them for when I had to call people back. That's how it was done. Today, it's done quite a bit different. You have lists of people, you get their email address, and you send massive email out to them. If they're in the market, they respond. If they're not in the market, they don't look at the email.

Also, I try to keep people going. Once we've done a deal for them, they have a relationship with us. So unfortunately, lease goes by and it's seven years, 10 years. They don't even remember you anymore. They don't know you got 10 months of free rent and 15% below the market price of that space. So you got to keep on reinforcing yourself.

So I write articles every week to my brokers of like 10 different things going on in the industry. We pull these out of all these different periodicals. So they need to send these articles to their customers and say, "By the way, this is an update." So it reminds them.

How this happened with me is that I moved to an advertising agency, and I said they took 20% more space. I called the guy, "What happened?" He said, "Norman, I couldn't remember your name. I couldn't find your name." So I learned that you got to somehow send out a monthly newsletter or something giving people an update.

It's interesting. I did a deal downtown and a tenant said, "Norman, we haven't spoken. I couldn't remember your name. I put the word real estate in my emails, and your name came up." They called me up to redo their lease. It was in a Larry Silverstein building downtown. It was like 26,000 square feet. It was like a very easy deal for me to do because they wanted to keep the tenant. Our customer had no idea what they were entitled to. I got them a fabulous deal. It was good for Larry's building, and it was good for the customer.

But you have to have that drive. You have to enjoy what you do. But you have to get over your hangups. Again, you have to come to the office. In brokerage, you have to be self-motivated. They're not sitting there waiting for them to call you. You have to call them. So you have to come to the office and say, "I'm going to make 50 calls today. I'm going to make 30 calls."

You have to work on Fridays. You know, I'm here this Friday, we're doing this. I enjoy coming to the office. I enjoy the brain stimulation and figuring out problems. You have to enjoy what you do. I mean, you got your weekends, you got your holidays, and you have your vacation time. But you really have to enjoy what you do.

The bottom line is to have goals for your money. Your money, again, as I said earlier, is not just to have another house and another house and another house. No. How can you help somebody out there, whether you're helping the blind or whether you're helping someone get their education? Because I do scholarships for a school. Let me tell you, when you see how heartbreaking some of these people are with their problems, you know what you're doing is really great.

There are a lot of people that do a lot of great things out there, and you want to be part of them. You want to be one of those people.

Aaron Strauss: Well said. I know you've also, on the investing side, been involved by watching your father and then being a syndicator yourself of many, many different investments. I know we've talked as well where you've really stepped up. Maybe one random investment doesn't do as well as the others. You take it upon yourself personally to make sure that it does. I mean, you've stretched yourself to make sure that your word is your bond, that you show up for people.

Maybe you can describe how you balance that side of the business. I know you've got other people with you on that side, and we could touch on the franchise side a little bit perhaps, but you also have to manage the whole brokerage dynamic. So how do you keep it all going in real time and figure out where to spend your time on any given day?

Norman Bobrow: Yeah. So I am a deal, what do you call it, a deal junkie, you got to say, but I love doing deals. Again, the money I make, quite a bit goes into my foundation, which again, will be a lot bigger when I die because a lot of my money will go into the foundation. It's for education mostly, that's my biggest role. But I was very lucky to have a father that showed me these investments.

My son came into the business, but he said, "Dad, I can't be a broker. I can't do this negotiating. I feel like I'm lying." No matter how much I told him, "You're not lying. You're just negotiating to get the best price for a tenant. You're not lying, but you have to get the landlord down, and you got the tenant to come up. You got to negotiate." So I was lucky enough that a bunch of properties came in. We were able to buy these properties at a very good profit margin. He took on that management.

I also have two sons-in-law, where it became so big on the investment side that they joined. So I do have an arm of the business, which is investing. My investment arm became really very unique. God put a guy next door to me, a next-door neighbor, who moved into the house next door. We drove him one day. He says, "I run franchises." I said, "Well, I do investment deals, which are about 7%, 8%, 9% return." He said, "Well, mine are operating businesses, and we make 14%, 15% return."

So I gave him some money. I did one or two deals with him. Then after that, I said, "I'll give you a lot more money." He said, "Norman, I don't want to raise money for my deals. I love to do the deals, but I don't want to raise the money." Basically, he had me raise the money, and deals actually turned out to be about an average of about a 25% return. So I was very interested in how to keep my customers always in tune with me.

You do a lease for someone for 25,000 feet, and there's everybody after that tenant. So I brought my customers into these deals, and I said, "Look, I'll guarantee your money for two years. If something goes wrong or you want to get out, I'll give you your money back after two years."

But when they saw those checks coming in on a quarterly or monthly basis, suddenly, I was the best call they ever got. If I called someone, they got rid of all the other calls, "Okay, Norman, I'll commit to $50,000. I'll commit to $200,000. I'll commit to $500,000." So I was very lucky to ever do these deals.

I'll give you one story. We got a guy who wants to sell 14 shopping centers with self-liquidating mortgages on all the properties. So it was too big for me. I went to a big real estate family, the Rosen family, in the city. They said, "Oh, Norman, we love this deal." I said, "Well, I want you to take a piece of it because I want your advice." I like to have partners because we sometimes brainstorm on things. I put 32 people into this deal, which was a major multi-million dollar deal in North Carolina, South Carolina, and Georgia. Now the people are still getting their 16% return, probably more because we've turned equity back.

But it shows you that things can turn out well if you know what you're doing. Again, I have the experience of seeing these things. The operating deals, as I said, 25% return. They got up to a 35% return. Then the partner suddenly said, "Norman, I want to retire. I'm giving my money basically away to charity. My wife has enough. My second family has enough. I'm giving a lot to charity." So I tried to take over whatever I could, and things were liquidated.

I have all these now residential deals that I did with some of the biggest people. I don't put more than too much in any one deal. I always tell people, "Don't put more than 5% in any one investment, no matter how good it looks, how great it looks." I'll give you one little story. There was a new project being built in Florida in a beautiful location. A builder was building out these two buildings. When it was totally built, beautiful condition, floor-to-ceiling glass apartments, my brother flew down. He's a physician, but his head's been in real estate his whole life.

He said, "Norman, the rents they're getting today are higher than those projections." So we took a big piece of this deal. Then the other building that was being finished, we were renting that at the same time. Interest rates went berserk. In four months, they doubled. That person, who's a very experienced guy, couldn't lock in the interest rates. Now we're sitting with "what should we do here?" No one's getting a return on their money. Yes, the place is totally occupied, but it's a nightmare.

As Aaron was mentioning, yes, I did have a capital call and money had to be put up, and I put up all the money for all my 37 investors. So I wouldn't have to tell people, "You have to contribute this or that." I said, "I'll lay out the money interest-free." But what happens is sometimes things don't work out. So never, ever, no matter how something looks good, put more than 5% of your net worth in any one deal. That's always been my policy. That was something I made up, just basically listening to people like Warren Buffett, who said, "I made many mistakes and I lost plenty of money, but the good ones were so good that they made up for anything that was bad."

I remember one person telling me, "Norman, we lost this deal; this turned out to be a disaster." I said, "How about the other 14 deals you're in?" So yes, I'm in over 100 investments in 27, 30 states. I'd say 90% are doing great, but 10% are really lacking. It's all because of that hiccup we had out there during the interest rate debacle.

Aaron Strauss: Well said. You've got a lot going on, and you're running and gunning every day. I love it. Love the vibe and energy in the office. How about just a snapshot of what's going on today? I mean, you're in a tried and true business. What's really cool about brokerage is its relationships and knowledge, and integrity, which you combine beautifully.

Technology is coming in, but it's hard to have technology replace human interaction and doing tours, and the like, and having off-market knowledge. But what do you think is going to be the most critical element of success in the next one to five years beyond the normal tried and true items we've already been discussing? How do you think the new normal is going to shake out with technology changing everything, markets changing? What's exciting for you and what's scary today?

Norman Bobrow: Years ago when we did a survey, just to give you an idea of how difficult it was, we had 20 books in the office. One was Madison Avenue, Fifth Avenue, Park Avenue. Then we had books that were cross-streets. Then we had books that were by landlord. So when you did a survey for someone, "I need 10,000 feet and I'd like to be between Fifth Avenue or Sixth Avenue and Park Avenue between 50th and 60th Street," we had to go through 10 books to look at all those listings.

We also had to have a person here, the mailman would come with a sack of mail every week with new listings. So I have a person just updating those listings, stamping them in when it came in, taking out the old listings for those buildings. There used to be a firm called Cross & Brown, they'd send out their own book of the listings. So you'd have to know that they had 622 Fifth Avenue, that they had 292 Madison. You'd have to know all these different places.

Today, it is so much easier. You go into CoStar, you could put a north boundary, a south boundary, an east and a west boundary. You put the price range, you put everything in here, and then you push a button and it gave you all the different spaces. But a smart broker will also sit there and call individual buildings. "You know what? This building shows nothing here. I'm going to call 500 Fifth Avenue. I'm going to call One Penn Plaza." I'm going to actually call those buildings because that's a good building in that area.

But a good broker looks at the spaces. Like, Aaron, you say you need 10,000 feet. I'm not going to throw you all these spaces. I'm going to go look at those spaces. Now, when you're in the business for a long time, you know what every space in One Penn Plaza looks like. You know it's a center core building. You know that there's a corridor going around the entire outside of the building. You know, does it face water views or does it face city views? So basically, you do your homework and you get better and better.

Like I do preview almost every space I show to a tenant, but a lot of buildings, if I'm showing something in the Empire State Building, I know on the 32nd floor, I'm getting panoramic views from everywhere I look. I know I'm getting seven or eight or 10 windowed offices, corner offices on every floor. I don't need to go and preview that. But what is also simple, again, is that all of these spaces, they have a tour on the computer.

I guess the hardest part is you have to hear someone's requirement and be able to say what would be good for them. So you go to the doctor and you go and say, "Look, I'm having some pains in my chin." He diagnoses you. So the broker is the doctor. We hear your situation, and we got to give you the best advice. Sometimes it's saying, "I got to show you something two blocks further north. I have to show you something further west."

I can tell you that I've done at least 10 deals where I've been in someone's office and said, "Can you look at the space right now? I have something right now that I think would be ideal." In those tenants, I've shown one piece of space, one location, because it was so pinpointed. But the only way you get this is that you put your time in, you see the spaces, you know the market, you know who the landlords are, you know who's flexible, who can build, who can't build.

You know your customer. Like we're doing a lease now for a law firm, and he was very sensitive on the security deposit. He also didn't want to deal with a letter of credit. We got him a three-month cash deposit. Unfortunately, we were dealing on a Third Avenue building, which the landlord was being ridiculous. Now we're putting them on Madison Avenue with a much better deal, much cheaper deal.

The tenant said, "I'm listening to you. Let me see what you're saying." You have to trust him. So when you go to that doctor, he's the professional. When you go to your accountant, he does your taxes. You know, you go to one accountant, one doctor. So you really need to hire one broker that you know is going to really hustle for you and knows what they're doing. That's what we try to train our people here, that they are smart out there and that they work.

Aaron Strauss: Well said, Norman. We've covered a lot. I don't want to keep you all day. I want to thank you for making the time. I always learn from you when we hang out on life, on real estate, on charitable items, and communal work. You're really just what I call hitting for the triple crown, if you will. You're doing it all. You're very humble about what you've done. I know you make time for everybody, which is incredible.

So I guess we'll wrap here. I continue to be close with you and follow what you're doing. If people want to look you up, obviously, we're going to share all your information. You've really built an incredible name for yourself, which is predicated on all the right pillars you want to be associated with. So amazing work.

Norman Bobrow: Well, Aaron, I have to tell you that dealing with you has always been first class and smart, very smart. You've helped me bring the deals to making them happen. When there was a problem, you'll handle it, or I'll handle it. So I have to say thank you for who you are and your abilities to help us.

Aaron Strauss: Well, Norman, I appreciate you so much. With that, we'll wrap. Thank you again so much. Thank you for joining The Dealmakers' Edge. Don't forget to follow us on your favorite podcast platform. Please, give us a five-star rating so more people can follow the conversation.